I can’t quantify the risk, and I hope that ability to quantify it comes with experience and a bigger/better network.Sounds like you’ve got a good handle on things.  

Make sure to consult with your CPA about which hours can be used before starting your hours log.Here are the indicators that put you at risk of an Audit that the IRS looks at with this strategy::(Source)Real Estate ProfessionalIf you don’t have the ability to invest these kinds of hours into a property, you can become a Real Estate Professional under the tax code, or have a wife or husband become a Real Estate Professional, which then will turn your Passive Losses into Active Losses on your real estate.To become a Real Estate Professional, you need to have:(Source)As long as you work 750 hours in real estate (14.42 hours a week excluding vacation), AND half your time is spent on real estate activities (so you could still do other work for 12-13 hours a week), you can qualify as a Real Estate Professional.

We have the education, we have the clients, we have the ability to learn from eachother in the investing space better than any other community.

I'm a big believer that house hacking a multi with a conventional loan is the best way to start, so I'd be finding an investor friendly agent who you click with, talking to a lender and seeing what you can do within your abilities and relative comfort level. 

I feel confident in my ability to handle a lot of the work, but I also want to be realistic about lender requirements.Another thing I’m unsure about is whether building an A-frame specifically is much more expensive than a traditional home.

These two elements often get overlooked in the excitement of deal-making, but they play a critical role in the long-term success and sustainability of your investment journey.A well-thought-out tax strategy helps ensure you're maximizing all available deductions, utilizing the most favorable tax structures, and ultimately keeping more of your hard-earned income.

@Jules Aton we agree with Account ClosedA reputable PMC should be using Property Management software to properly manage rentals.Every PMC sofware we've looked at has built-in accounting with the ability to generate invoices.

For example: Does living in one unit affect your ability to refinance for BRRRR?

You essentially give up your ability to be a fiduciary when you do these deals and there's no value you can bring to your client, only the wholsaler wins. 

Just remember it’s only a timing play—you’re pulling deductions forward into year one, which means less left in future years—and your ability to use them depends on passive activity rules.